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+
+
K HA
H
K
H
a
a
[ ]
[ ]
[ ]
1
1
D =
[HA]
[HA]
2
1
1+
+
K
H
a
[ ]
=K
Sol vent Ex t r ac t i on (pH ef f ec t s)
D =K 1+
+
K
H
a
[ ]
D=
K
1+
=
+
+
+
+
K
H
K H
H K
a a
[ ]
[ ]
[ ]
D
pH
[H
+
]=K
a
pH=pK
a
K
[H
+
]>>K
a
mainly
HA
[H
+
]<<K
a
mainly
A
-
Sol vent Ex t r ac t i on (pH ef f ec t s)
pH effect on D for organic acids
K
1
4 8
K
2
D
pH
Sol vent Ex t r ac t i on (pH ef f ec t s)
Example problem: Want to separate two
organic acids using a scheme based on pH.
Acid 1 (pKa= 4), Acid 2 (pKa= 8)
Acid 2 stays in
organic phase,
acid 1 is extracted
into aqueous phase
[H
+
] + K
a
D =
K K
a
D
pH
K
[H
+
]=K
a
pH=pK
a
[H
+
]>>K
a
mainly
BH
+
[H
+
]<<K
a
mainly
B
Sol vent Ex t r ac t i on (pH ef f ec t s)
Analogous treatment for organic bases
(proton acceptors, not KOH)
D
pH
K
acid
base
Sol vent Ex t r ac t i on (pH ef f ec t s)
In general:
Initial Aq. phase
Aq. Phase
Org. acid
Aq. Phase
Org. base
Ether Phase
Org. acid, Org. neutral
Ether Phase
Org. neutral
pH=1, extract with ether
extract with pH=12 Aq. Soln
Separ at e or gani c ac i d, base
and neut r al anal yt es
Cal c ul at i ons
Determine K
D
for extraction of solid
in the two solvents
) ( / ) (
) ( / ) (
mL water g unk
mL solvent g unk
K
D
=
Pr ac t i c e Cal c ul at i ons
Mass solid 120 mg
Total volume organic solvent 1.5 mL
Total volume water 1.5 mL
Mass solid extracted into
organic solvent
92 mg
Mass remaining in water 120-92 = 28 mg
K
D
= 92 mg/1.5 mL
28 mg/1.5 mL
= 3.3
Yes, I am f ul l , c onf used
Take a little break?
Yo, wis semene dhisik..